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Literature summary for 3.4.21.98 extracted from

  • Baeck, M.; Johansson, P.O.; Wangsell, F.; Thorstensson, F.; Kvarnstroem, I.; Ayesa, S.; Waehling, H.; Pelcman, M.; Jansson, K.; Lindstroem, S.; Wallberg, H.; Classon, B.; Rydergard, C.; Vrang, L.; Hamelink, E.; Hallberg, A.; Rosenquist, S.; Samuelsson, B.
    Novel potent macrocyclic inhibitors of the hepatitis C virus NS3 protease: use of cyclopentane and cyclopentene P2-motifs (2007), Bioorg. Med. Chem., 15, 7184-7202.
    View publication on PubMed
Search for more literature for 3.4.21.98

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Huh-7 cells Hepacivirus C

Inhibitors

Inhibitors Comment Organism Structure
(Z)-(1R,4R,6S,14R,16R)-12-tert-butoxycarbonylamino-16-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,13-dioxo-3,12-diaza-tricyclo[12.3.0. 04, 6]heptadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,15R,17R)-13-amino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,15R,17R)-13-tert-butoxycarbonylamino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,15R,17R)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,15R,17S)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,16R,18R)-14-amino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,16R,18R)-14-tert-butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,17R) and (1S,4R,6S,17S)-13-amino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadeca-7,15-diene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,17R,19R)-15-amino-19-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,16-dioxo-3,15-diaza-tricyclo[15.3.0.04,6]icos-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,17R,19R)-15-tert-butoxycarbonylamino-19-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,16-dioxo-3,15-diaza-tricyclo[15.3.0.04,6]icos-7-ene-4-carboxylic acid
-
 Hepacivirus C
(Z)-(1R,4R,6S,18R) and (1S,4R,6S,18S)-14-amino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04,6]nonadeca-7,16-diene-4-carboxylic acid
-
 Hepacivirus C
BILN 2061
-
 Hepacivirus C
cyclopropanesulfonic acid [(Z)-(1R,4R,6S,15R,17R)-13-amino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-amide
-
 Hepacivirus C
cyclopropanesulfonic acid [(Z)-(1R,4R,6S,15R,17R)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-amide high potency, lacks the P4 substituent Hepacivirus C
cyclopropanesulfonic acid [(Z)-(1R,4R,6S,15R,17S)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0. 04,6]octadec-7-ene-4-carbonyl]-amide
-
 Hepacivirus C
additional information 14-membered ring system is the most potent.The corresponding 13-, 15-, and 16-membered macrocyclic rings deliver less potent inhibitors. Corresponding P1 acylsulfonamides have superior potencies over the corresponding P1 carboxylic acids. Highly potent protease inhibitors lack the P4 substituent Hepacivirus C
[(Z)-(1R,4R,6S,15R,17R)-4-cyclopropanesulfonylaminocarbonyl-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-en-13-yl]-carbamic acid tert-butyl ester
-
 Hepacivirus C

Organism

Organism UniProt Comment Textmining
Hepacivirus C
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Ac-Asp-Glu-Asp(EDANS)-Glu-Glu-Abu-psi-(COO)Ala-Ser-Lys(DABCYL)-NH2 + H2O
-
 Hepacivirus C ?
-
 ?

Synonyms

Synonyms Comment Organism
NS3 protease
-
 Hepacivirus C
NS3/4A protease
-
 Hepacivirus C

Cofactor

Cofactor Comment Organism Structure
additional information NS4A cofactor peptide Hepacivirus C

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000000091
-
 cyclopropanesulfonic acid [(Z)-(1R,4R,6S,15R,17R)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-amide
-
 Hepacivirus C
0.00000007
-
 [(Z)-(1R,4R,6S,15R,17R)-4-cyclopropanesulfonylaminocarbonyl-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-en-13-yl]-carbamic acid tert-butyl ester
-
 Hepacivirus C
0.00000019
-
 cyclopropanesulfonic acid [(Z)-(1R,4R,6S,15R,17R)-13-amino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-amide
-
 Hepacivirus C
0.0000044
-
 cyclopropanesulfonic acid [(Z)-(1R,4R,6S,15R,17S)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0. 04,6]octadec-7-ene-4-carbonyl]-amide
-
 Hepacivirus C
0.000006
-
 (Z)-(1R,4R,6S,15R,17R)-13-amino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.000015
-
 (Z)-(1R,4R,6S,17R) and (1S,4R,6S,17S)-13-amino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadeca-7,15-diene-4-carboxylic acid
-
 Hepacivirus C
0.000031
-
 (Z)-(1R,4R,6S,15R,17R)-13-tert-butoxycarbonylamino-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.000044
-
 (Z)-(1R,4R,6S,15R,17R)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.00011
-
 (Z)-(1R,4R,6S,18R) and (1S,4R,6S,18S)-14-amino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04,6]nonadeca-7,16-diene-4-carboxylic acid
-
 Hepacivirus C
0.00012
-
 (Z)-(1R,4R,6S,16R,18R)-14-amino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.00013
-
 (Z)-(1R,4R,6S,14R,16R)-12-tert-butoxycarbonylamino-16-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,13-dioxo-3,12-diaza-tricyclo[12.3.0. 04, 6]heptadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.00026
-
 (Z)-(1R,4R,6S,15R,17S)-17-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,14-dioxo-3,13-diaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.00071
-
 (Z)-(1R,4R,6S,16R,18R)-14-tert-butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.01
-
 (Z)-(1R,4R,6S,17R,19R)-15-tert-butoxycarbonylamino-19-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,16-dioxo-3,15-diaza-tricyclo[15.3.0.04,6]icos-7-ene-4-carboxylic acid
-
 Hepacivirus C
0.01
-
 (Z)-(1R,4R,6S,17R,19R)-15-amino-19-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,16-dioxo-3,15-diaza-tricyclo[15.3.0.04,6]icos-7-ene-4-carboxylic acid
-
 Hepacivirus C